1-Bromo-3-chloropropane → 8-(3-Chloro-propoxy)-5,6-dihydro-3H-benzo[f]cinnolin-2-one

HRID 2042643Notes

Reaction equation

HRID 2042643 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[C:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)=[N:10][NH:9][C:8](=[O:14])[CH:7]=3.Br[CH2:18][CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[C:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)=[N:10][NH:9][C:8](=[O:14])[CH:7]=3

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 596519348-hydroxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Product 1

HCID 596519478-(3-Chloro-propoxy)-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 50 mL round bottom flask, 8-hydroxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one (575 mg, 2.69 mmol), 1-bromo-3-chloro-propane (0.27 mL, 2.69 mmol), and potassium carbonate (371 mg, 2.69 mmol) in acetonitrile (20 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated, dried over MgSO4. Purification with silica gel chromatography eluting with methylene chloride/methanol (95:5) produced 106 mg (14%) as an amorphous solid. MS m/z 291 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with methylene chloride/methanol (95:5)
  9. customproduced 106 mg (14%) as an amorphous solid

Sources & evidence

ORD record
ord-4e55530c499240718871c3f957615b19
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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